Author: Randy

LegalMation — Walking Into Someone Else’s Pipeline Mess

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After Yext, I went smaller and scrappier on purpose: VP of Sales at an AI legal-automation startup, brought in specifically to fix a sales organization that badly needed fixing.

“Needed fixing” is generous. What I actually inherited was a pipeline that had been represented far more optimistically than reality supported, forecasting that couldn’t be trusted, and effectively zero qualification discipline. Nobody had been asking the hard questions on any of these deals — who the actual economic buyer was, what the real decision process looked like, whether there was a champion who’d still be there next quarter. #GutCheck

First move, and this will sound familiar if you’ve been following along: MEDDPICC. Same qualification discipline I first implemented as a Business Unit Executive rebuilding IBM’s Great West territory back in 2010, just with two more letters added over fifteen years of sales methodology evolving. Funny how the fix for “we don’t actually know if we have a deal” hasn’t changed much — you still have to force the same honest answers out of every opportunity, no matter how much the product or the era has changed around it. #SomeThingsDontChange

Second move was repositioning the whole motion. The team had been selling almost exclusively the easiest entry point into the product — Complaint Response — when there was a full AI workflow portfolio sitting right behind it: Discovery Response, Deposition Assistant, Demand Letter Response, Matter Profiling. Once the ideal customer profile and buyer personas were actually clear — General Counsel, litigation partners, insurance carriers, legal operations teams — the broader portfolio became a much easier sell than anyone had been treating it as. Between the qualification discipline and the repositioning, we identified $19M+ in new pipeline that either hadn’t existed on paper or hadn’t been properly qualified before.

The piece of this chapter I’m most proud of, though, is one I built from nothing: I established the Microsoft Azure partnership and got LegalMation listed on Azure Marketplace. For a startup that size, that’s not a checkbox — it’s a different sales motion entirely. Once we were listed, enterprise legal and IT buyers could procure LegalMation against Azure spend commitments they’d already made, which cuts through a huge amount of the approval friction that normally kills deals with a small, unproven vendor. It also bought something a startup can’t manufacture any other way: instant credibility. Walking into a General Counsel’s office with a live Microsoft partnership behind you changes the conversation before you’ve said a word about the product. #FullCircle — the marketplace muscle I built selling Oracle and NetApp through hyperscalers turned out to be exactly what a scrappy legal-tech startup needed most.

If I’m honest about why that chapter wrapped at eight months: turnarounds like this take real time to fully convert into closed revenue, even once the pipeline itself is genuinely healthy again — and fast-moving startup timelines don’t always leave room for that runway. It was a clarifying lesson more than a disappointing one: the right fix still needs the right amount of time to prove itself out, and I’m proud of the sales foundation I left behind either way. #RightFixWrongClock

That’s the last chapter before the most recent one, which is a different animal altogether — public sector, and a restructuring that ended it. That one’s next, whenever you’re ready.

#LegalMation #MEDDPICC #Azure #LegalTech #AI

Yext — A Marketing Platform “MarTech”, a Player-Coach Role, and a new focus on Healthcare

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After NetApp, I did something I hadn’t really done before: I left infrastructure entirely.

Oracle, IBM, NetApp — whatever the specific product, I’d spent two decades selling things that lived in a data center or a cloud console. Storage, compute, databases, analytics engines. Yext is none of that. Yext is a digital presence platform — it manages the “knowledge graph” of facts about a brand (locations, hours, providers, services) and makes sure that information shows up correctly everywhere a customer might look for it: Google, Apple Maps, review sites, and increasingly, whatever AI tool someone’s asking instead of searching. #NewCategory

In healthcare specifically, that’s a bigger deal than it sounds. Get a location’s hours wrong, or list the wrong doctor at the wrong clinic, and you’re not just annoying a customer — you’re potentially sending a patient to the wrong building. Selling that story meant a whole new pitch, to a whole new buyer: not IT, but marketing and brand leaders who think in terms of patient acquisition and experience, not uptime and throughput. Different room, different language, same job of finding the pain and proving you can fix it. #NewPitch

I came in as Director of Sales for Healthcare in the Western US — but as a player-coach, which meant carrying my own quota while also mentoring a team carrying theirs. I hadn’t done that particular juggling act in a while, and it’s a genuinely different rhythm: you’re closing your own deals and reviewing theirs, in the same week, sometimes the same day. Delivered 120% of my individual number and generated $25M+ in pipeline.

The bigger structural move was rebuilding the Western US territory into an actual top-50 strategic account plan across healthcare payers and providers, instead of whatever list had accumulated over the years. That discipline paid off in wins with Humana, Scripps, Kaiser Permanente, HonorHealth, and El Camino Health — a mix of payer and provider logos that, frankly, I was proud to have across one territory plan.

A year into it, a different kind of pull showed up — not a bigger territory or a new vertical this time, but a much smaller company that needed something I’d been building a reputation for since my Great West days at IBM: actual sales discipline, from the ground up. That’s next.

#Yext #DigitalPresence #Healthcare #PlayerCoach

#NetApp — Trading a $100M Account for Four Very Different Ones

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After two years caring for (in the best possible way) one of Oracle’s biggest life sciences relationships, I made a jump that looked backwards on paper and turned out to be exactly the stretch I needed: Client Director at NetApp, December 2021.

Instead of one giant account, I picked up four — an energy utility, an automotive manufacturer, an investment/wealth management firm, and a life sciences company, all in Southern California, all completely different animals. If Oracle had taught me how to go deep on one relationship, NetApp was about to teach me how to go deep on four at once, in four industries that don’t share a single vocabulary. #RangeOverDepth

The account that ended up defining the chapter was Southern California Edison — a name most people know as “SCE” and not much else, until you’re inside their infrastructure conversations and realize how much of what keeps the lights on in this paart of the state runs through decisions made in rooms like the ones I was suddenly sitting in. Capital Group was the other big one — completely different risk profile, completely different definition of “uptime,” completely different buying committee. Two accounts, same building block (NetApp storage), two entirely different sales.

The real work, though — the actual “rebuild” part — was less about winning anything new and more about changing the conversation. NetApp walked into most of these accounts known as a storage vendor. My job was getting the same people who’d been buying arrays and shelves for a decade to start talking to me about cloud, SaaS, hyperscaler integration, and business continuity instead. That’s a slower sell than it sounds — you’re not pitching a new product, you’re asking someone to reclassify what they think you’re for. #NotJustHardware

It worked out: 180% of target in FY22 2H, 210% in FY23 1H — and more importantly, conversations that used to start and end with “how much storage do you need this quarter” started including cloud strategy and resilience planning instead.

Two and a half years in, another opportunity pulled me toward something I hadn’t done in a while: getting back into a pure healthcare vertical, and picking up an individual quota again alongside leading a team. That’s next.

#NetApp #MultiCloud #SoCal #AccountManagement